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4-Chloro-3-nitrobenzoic acid → 2-Methyl-1,3-benzothiazole-5-carboxylic acid

HRID 1498958
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1498958
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-])=O.O.O.O.O.O.O.O.O.O.[S-2:23].[Na+].[Na+].C(O[C:30](=O)[CH3:31])(=O)C>C(OCC)(=O)C.O.C(O)(=O)C>[CH3:31][C:30]1[S:23][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 73204-Chloro-3-nitrobenzoic acidHCID 7918Acetic AnhydrideHCID 73972Sodium sulfide nonahydrate

Produkt 1

HCID 6499532-Methyl-1,3-benzothiazole-5-carboxylic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittel
HCID 962
Water
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Chloro-3-nitrobenzoic acid (2.02 g, 10.00 mmol), sodium sulfide nonahydrate (7.22 g, 30.00 mmol) and water (5 ml) were suspended, and the mixture was heated at about 100° C. for 30 minutes. After being allowed to cool, the mixture was cooled by ice, and acetic anhydride (18 ml) and acetic acid (10 ml) were added to the mixture. The resulting mixture was heated under reflux for 2 hours and stirred at a room temperature for 15 hours. To the mixture, tap water and then ethyl acetate were added, and sulfur was removed by filtration. The ethyl acetate layer was washed with a saturated saline solution, and then dried over anhydrous magnesium sulfate and concentrated to give the title compound (1.54 g, 80%) as a light-yellow powder.

Aufarbeitung

  1. temperatureto cool
  2. additionwere added to the mixture
  3. temperatureThe resulting mixture was heated
  4. temperatureunder reflux for 2 hours
  5. customsulfur was removed by filtration
  6. washThe ethyl acetate layer was washed with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0b5aa2b412a340c1bda4f6fd0695096c
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09200008B2

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